Nu-soya nu-ethyl morpholinium ethosulfate cosmetic emulsions



United States Patent N-SOYA N-ETHYL MORPHOLINIUM ETHO- SULFATE COSMETIC EMULSIONS Walter A. Taylor, Clinton, Conn., assignor to Chesebrough-Ponds Inc., a corporation of New York No Drawing. Application August 28, 1953 Serial No. 377,231

14 Claims. (Cl. 167-90) ly associated with underlying structures of the body and yet serves as the principal body contact with its external environment. It consists of a connective tissue framework, with blood vessels, lymphatics and nerves, and a covering of epithelium, the outer layer of which is known as the stratum corneum and it consists of a plaque or layers of keratin. The most important function of the skin is the protection it provides the body. Mechanical protection is obtained principally by the arrangement and distribution of subcutaneous fat tissue which acts as a spongy cushion. In addition, the epidermis or outer layers are relatively tough and resistant to traumatic injury. The skin is a very poor conductor of radiant energy; and, therefore, protects the body against light, heat and electric radiation injury. The fatty matter deposited in the stratum corneum prevents rapid evaporation of the fluids from the body and the impermeability of the skin prevents damage from the absorption of too much fluid. The keratin outer layer offers resistance to chemicals while the coherence of the cells in the granular layer and their fatty matter offer resistance to penetration of the skin by bacteria. The sweat glands and the pile-sebaceous system provide the slightly acid sweat secretion and the fatty sebum which supply protection not given by the relatively thin outer epithelial covering. Thus, the secretion accomplished through the sebaceous and sweat (coil) glands, furnishes oil and moisture to render the skin soft and pliable; and, to a degree, eliminates waste products. The sebum from the sebaceous gland anoints the greater part of the skin surface with oil. The moisture is secreted by the sweat glands primarily to regulate temperature; and, to some extent, these glands function as excretory organs. It supplies moisture to the surface, however, to give pliability to the skin and also supplies a fungicidal and bacteriocidal agent to counteract microbial invasion.

The normal functioning of the skin may be disturbed by a number of factors. The keratolytic or slough rate and the germinative action or growth rate may become unequalized. An excessive keratin persistence on the gland openings may result which will cause keratin plugs or comedones to form over or in the gland ducts and cysts may also form. If the slough rate is decreased a dry, hard, horny excess of keratin will form on the outer surface resulting in calloused skin. The skin, in either event, will become rough, dry and irritated. The oil and water content of the interspaces of the stratum mucosum may be reduced by either external environment or internal conditions and cause irritation. The activity of the sweat and sebaceous glands may be diminished or the normal functioning of the stratum germinativum may be reduced; and, in either case, skin irritation will result. The skin may also become irritated when exposed to water too frequently or to alkaline materials; such as, for example, alkaline soaps and detergents having a pH in the range of from about 8.0 to 10.00. In all cases of skin irritation the blood vessels in the vascular bed beneath the epidermis become engorged to overcome the irritation. This results in skin redness and the inflammation produced below the epidermis may result in an itching sensation.

Many cosmetic preparations have been prepared with the view to overcoming skin irritation and restoring the skin to a soft pliable state. Such preparations have included emollients; and, in many instances, surface tension reducing agents have been utilized to enhance the penetration of the preparation into the skin. These preparations have never been wholly satisfactory because of the impermeability of skin to ordinary water and to chemicals in solution, particularly in skin where a condition of excessive keratin persistence in the stratum corneum exists. Fats and chemicals incorporated in fats are absorbed to some degree as, also, are the fat solvents; such as, for example, alcohol, ether and benzene. Some hormones and vitamins when applied in oil solution may be absorbed. Heretoforc, the absorption of prior known preparations into the skin in amounts suflicient to serve any useful purpose has been precluded by keratin persistence in the epidermis.

It is the principal object of this invention to provide a stable acidic emulsion base which is a keratolytic agent and a stimulant for the sweat and sebaceous glands and the stratum germinativum. Another object of this invention is to provide an emulsion base capable of counteracting and preventing alkali and water trauma of the skin. Still another object of this invention is to provide an emulsion base which alone or in conjunction with emollient materials will supply oil and water to the interspaces of the stratum mucosum. A further object of this invention is to provide an emulsion base having a pleasant odor and appearance, a good consistency without being oily and sticky and which is stable for long periods of time even when subjected to relatively high temperatures.

The objection to preparations for treating the skin which have been heretofore employed are overcome and the foregoing objects are accomplished by this invention which is based upon the discovery that N-soya N-ethyl morpholinium ethosulfate is mildly irritating to the skin, without being destructive, and that an aqueous emulsion of N-soya N-ethyl morpholinium ethosulfate and an acid stabilized partial ester of a saturated or unsaturated higher fatty acid and a polyhydric alcohol or ether; such as, for example, an acid stabilized glycerine monostearate, propylene glycol monostearate, or diethylene glycol monostearate possess unusual dermatological characteristics. These emulsions or emulsion bases possess the unique .properties of being keratolytic agents and stimulants for the sweat and sebaceous glands and the stratum germinativum. The pH of the emulsion bases comprising this invention is in' the range of from about 3.0 to 4.0; and, therefore, these emulsions successfully counteract alkali irritation of the skin and prevent alkali-induced dermatitis or soap and water trauma. These emulsion bases will, alone supply oil and water to the stratum mucosum and .thus lubricate and restore softness and pliability to the .skin.

This function may be enhanced, however, and these desired results obtained more quickly, by incorporating a water soluble or an oil soluble emollient material the emulsion bases. Another advantage of these carbon atoms.

emulsion bases is that the acid stabilized mono ester and the quaternary amine salt cooperate to provide a product having a pleasant odor, a good appearance, and an excellent consistency. The surface ,tensionproperties-tot the two principalingredients cooperate,.to,provide..atlotionor a cream product having good viscositycharacteristics and which is neither too thin nontoo. oily aud.sticky when applied to .the, skin. The. emulsions are percutaneously .absorbed and penetrate the, mechanical, .electrical, and chemical barriers of the skin so thattheemulsion ingredients, including emollicnts whichmay be. employed therewith, pass through the dead outer layers oftissue and are brought into contact with theliving .tissueitself. The acid stabilized partial esters andthe quaternary amine salt furthermore cooperate, to provide an emulsion, base which is stable for periods as long as eighteemmonths, for ,onemonth 212,3. temperature of 100 F. and,for at least one weekpat, atemperatureof. 120 .F. 1 However, the ,rnostoutstanding advantages of these emulsionsare (1) that of being a keratolytic agent and capable, when introduced beneath the epidermis, of equalizing the keratolytic orsIough-Iate and the germinative or growth rate, and (2) that of having a stimulating'effect upon the sweat and sebaceous glands.

The acidstabilized emulsifying agents employed in the emulsion bases contain aliphatic polyhydroxycompounds partially esterified with fatty acids having from 12 to 18 The most suitable partial esters are the saturated or unsaturated highervfatty acid mono esters of polyhydric alcohols or ethers; such as, for example, glycerin monostearate, sorbitol monostearate, propylene glycol monostearate, and diethyleneglycolmonostearate. Other higherfatty acids may be employed in preparing the monoesters of these typical polyhydric compounds, such as, for example, lauric and palmitic acids. These esters areacid stabilized with hydrochloric or phosphoric acid salts of acylated diamines or carbon substituted or nitrogen alkylated .derivatives thereof. The acid stabilized mono ester or emulsifying .agent which is preferred in preparing the emulsions of this invention contains glycerine monostearate and from about 2,to about percent diethylaminoethyloleylamide phosphate. This may be prepared by mixing parts by weight of glycerine monostearate with 90 .parts by weight of water and 02 part by weight of diethylaminoethyloleylamide at 80.C. This is thoroughly agitated and is then permitted to cool. "In preparing the emulsions or emulsion bases .of this invention it is preferredto employ from'about3; to 'about' 10 percent by weight of the acid stabilized glycerine-monostearate. If a product having the characteristics and properties'of' a lotion is1desired the acid stabilized, glycerine monostearate will-be employed in amounts ranging' from about3 .to about S percent by weight. Fromahout Sto about '10 percent-by weight of the 'acid stabilized glycerine monostearate is employed if it is desired that the product have the characteristics of a softpaste cream. In a lotion-type preparation the preferred-amount is' about 4.5 percent by weight and, in a cream-typepreparation about 10 percent by weight'oftheacid,stabilized-glycerine monostearate is preferred.

The quaternary amine salt employed in preparing'the emulsions or emulsion basesof this invention is 'N-soya N-ethyl morpholinium ethosulfate. This, compoundis prepared from commercial distilled soyaLamine having the following general composition:

10 normal hexadecyl amine 10% normal ,octadecyl amine 35 normal octadecenyl amine .45 normal .octadecedienylzamine This starting material has an iodine-number '(Wijs) 50-- 60, titer'2834 C. andan apparentprimary-amine content of 96-98 percent. 'The material not primary amine is-secondary dialkyl amine. The amine is"reacted 'with an excess of technical dichlorethyletherinthe presence of an aqueous solution of sodium'carbonate,'theamount content should be less than 0.15 percent and the tertiary amine ,contentmust bebetween and theoretically. The hydrochloric acidequivalent is .the combining weight of N-soya morpholine as determined with hydrogen chloride. This :value is required to determine the stoichiometric amount of diethyl sulfate required to react with the N-soya morpholine andit ranges-between 350 and 380. The N-soya morpholine is then reacted with the stoichiometric amount of technical diethyl sulfate by heating at atop temperature. of C. to form N-soya N-ethyl morpholiniumethosulfate. Water is added until aconcentra'tionof35 to 40 percent is obtained and the pH is adjusted to"7.5-8'.0 with caustic soda. Activated carbon is added .and the solution filtered hot, cooled and adjuste'd to a concentration of'35 percent. It is preferred, in this invention, to employ the 35 percent aqueous N-soya N-ethyl .morpholinium ethosulfate but the anhydrous quaternary amine salt may be employed if desired.

"The dermatological properties'of' the N-soya N-ethyl morpholinium .ethosulfate .compounds obtained by the above method vary from batch'to batch even though identical starting materials-are employed. It is necessary, therefore, to subject each batch of N-soya N-ethyl morpholinium ethosulfate to biological. assay before: employing it'in the emulsions or emulsion bases of this invention. "This biological assay consists of an acute eye' irritation test upon albino rabbits which isperformed by introducing 0.1 ml. of a 1.0 percent aqueous solution offN-soya' N-ethyl morpholinium .ethosulfate each day into. the eye ofjthe rabbit. for a period of five days. If, atltheconclusion ,of this assay, there was no evidence of severeirritation .the f 35 percent aqueous N-soya, N-e'thyl morpholiniumethosulfate was found to be useful in the emulsions .of. this. invention.

Theamount of 35 percent aqueous N-soya N-ethyl morpholinium ethosulfate employed in preparing these emulsionsmayrange fromahout'OjO percent by weight to..not inexcess of..2.0 percent .by weight. The preferred .range;.is from -about 0.50 percent .by weight .to about 1.25 percentbyweightand it;is preferable to employ .ahout.l.0.percent,by weight of the .35 percent aqueous solution. of atheguaternary aminesalt. If too small .an amount .of the .quaternary .amine salt is employed the emulsion will be too thick and will lack heat stability. It also will not possess the desired dermatological properties. Amounts in excess of 2.0 percent do not increase the dermatological activity of the emulsions and maybe irritating. If the anhydrous N-soya N-ethyl morpholinium ethosulfate is employed the broad range of the amount thereof used should range between from about 0.17 percent by weight to about 0.70 percent by weight. 'I'hepreferred-range of anhydrous salt, however, is from,about.0.17 percent by weight to about 0.45 percent by weight and the ,best results have been obtained by yemploying about 0.35 .percentby weight of the salt.

The-emulsion bases of thisiuvention preferably :have

. incorporated therein fromabout 10.00 percent to about "such-a material. ,These emulsions. bring .an emollient into intimate contact with the tissue immediately and ac- .celeratc thepassage thereofthrough the dead-outer layers to:the living" tissueitself where it will assist in relieving .the'causes of idryness,."roughness' and redness; and, in cooperation with the emulsion base, tend to equalize the keratolyticrate andthegerminative action. Among the Water-soluble=emollients= which may beusecl are propylene glycol, sorbitol, glycerine, and sorbitan sesquioleate. The oil soluble emollients which may be used include such substances as, for example, lanolin, mineral oil, sesame oil, isopropyl myristate-palmitate, glyceryl monostearate, propylene glycol monolaurate, peach kernel oil and apricot kernel oil.

The emulsions or emulsion bases may contain other modifying ingredients to vary the properties of the product as desired. A small amount, about 0.75 percent by weight of pure. cetyl alcohol may be employed as a thickener. Cetyl alcohol also possesses some emollient properties. About 5 percent by weight of a 3 percent aqueous dispersion of hydroxy ethyl cellulose may be added to the emulsions as a thickener. Other surface tension reducing agents, such as, for example, Tween 80 and Span 80, the polyoxyethylene monooleate and monooleate esters of hexitol anhydride respectively, may be added to the emulsions in small amounts, about 0.2 percent; to less than about 2.0 percent and, preferably, about 0.2 to 1.0 percent. In order to prevent mold growth in the emulsions resulting from external contamination it is often desirable to incorporate from about 0.015 to 0.1 percent by weight of either propyl or butyl parahydroxy benzoate. Small amounts of coloring materials and a perfume, the characteristic odor of which is not suppressed or modified by the quaternary amine salt, may be added to the emulsion. In addition to the foregoing materials, it is possible to add medicaments; such as, for example, camphor, menthol, thymol and eucalyptol in small amounts to the emulsions. In most instances the total amount of medicament added does not exceed 2 percent and usually ranges between about 1 percent and 2 percent.

The emulsions of this invention; such as, for example, the emulsions of Examples I and 11 below, may be prepared by adding the acid stabilized glycerine monostearate to water, heating this to 212 F. and allowing it to boil for about five minutes. The heating is then stopped and the mixture allowed to cool to about 170 F. at which temperature the quaternary amine salt is added. This mixture is then stirred continuously and allowed to cool to about 140 F. When this temperature is reached the coloring materials and perfume may be added, the stirring and cooling then continued until the temperature reached about 120 F. at which temperature the stirring is discontinued. The preparation is thereupon allowed to stand and cool to room temperature. In preparing an emulsion containing either emollients or thickeners; such as, for example, the emulsions of Examples III through VIII below, the acid stabilized fatty acid monoester of the polyhydric alcohol or ether is added to water heated to 212 F. and thereafter allowed to cool to about 170 F. The emollients and thickeners may be mixed and heated to about 160 F. before adding them to the initially prepared mixture but it is preferred to prepare separate mixtures one of which contains the oil soluble emollients and thickeners and the other of which contains water, water soluble emollients and the quaternary amine salt, and then combine these mixtures. Thus, cetyl alcohol, sesame oil and isopropyl myristate-palmitate may be mixed and heated to about 160 F. Separately, propylene glycol may be added to water having a temperature of about 180 F. and the two ingredients thoroughly mixed. The quaternary amine salt is added to this mixture; and, with stirring, the mixture is cooled to about 160 F. The premixtures of oil soluble emollients and of water soluble emollients containing the quaternary amine salt are mixed; and, to the latter mixture, the mixture of the acid stabilized mono ester is added. A coloring material may be added at this stage if desired and, while the mass is maintained at a-temperature of about 150 F., the batch is passed through a colloid mill equipped with a cream head having a clearance of two thousandths. A perfume may be added when the batch has cooled to a temperature of about 140 F. and, thereafter the mixing is continued until the batch cools to a temperature of about F. The mixing is then discontinued and the batch is allowed to cool to room temperature.

The following examples are illustrative of the emulsions comprising this invention:

Example 1 7 This emulsion is a lotion having a smooth creamy consistency. It disappears rapidly when applied to the skinand does not produce an oily, sticky sensation. The 10-.

tion has a pH of 3.0 and it remained completely stable in oven tests for ten days at temperatures of 100 F. and.

F. This emulsion passes through the outer layer of skin very rapidly to provide a keratolytic action and stimulate the sweat and sebaceous glands. With repeated application to the skin this lotion cures redness, roughness and dryness of the skin. It also cures the damage caused by exposure of the skin to alkaline materials and prevents damage to the skin when alkaline materials such as detergents are brought into contact therewith. The keratolytic action of this lotion causes the dry, hard excess keratin to slough off and makes the skin smooth and pliable. If the anhydrous quaternary amine salt is used in this emulsion it is employed in the amount of 0.35 percent by weight and the amount of water employed is increased by 0.65 percent by weight.

Example II A cosmetic cream emulsion base having a soft plastic consistency was prepared by the above method from thefollowing ingredients in the proportions stated: 1

, Percent by weight N-soya N-ethyl morpholinium ethosulfate ,(35%

aqueous solution) 1.0 Acid stabilized glycerine monostearate 10.00. Water 88.80 Perfume-color solution 0.2

This emulsion base has a pH of 3.1 and is stable in oven tests at 100 F. and 120 F. for 10 days. It is a soft cream having excellent cosmetic properties; and, when applied to the skin, disappears readily when rubbed. Upon repeated application to the skin it demonstrates the same therapeutic activity as that obtained by the lotion described in Example I, above.

Example III A cosmetic cream emulsion containing emollients and a thickener was prepared by the method described hereinabove having the following composition:

. Percent by Weight N-soya N-ethyl morpholinium ethosulfate (35% The above preparation is a soft cream having a pH of 3.5 and it is stable in oven tests at 100 F. .and 120 F. for at least 10 days.

stimulant proper-ties demonstrated by the preparations of It possesses the same keratolytic and 7 Examples llan'dlhbnt; .due toy the: presencexoioihand watensolublei 'emollients, itiintroducesstoilsrintoa the interspaces of the stratumzmucosumzmorezquickly; and; there'- fore, :overcomesachapping, roughness; redness'anddryness of the skin very rapidly. In the aboveaernuls'ion' i3l5 percent by weight of the anhydrous N-soya N-ethyl morpholinium ethosulfate may be used in place of the aqueous product and the water content increased by 0.65 percent by welgiht' Example IV The cosmetic cream of Example III is an excellent carrierffor medicaments designed to treat the skin. A typical medicament mixture. which; may be. employed with the above emulsion .has the following. composition:

Partsby Weight Camphor 4 Menthol l Thymol. l

Medicated cosmetic creamsmay' be prepared which have the: following compositions:-

Parts by Weight Cosmetic cream emulsion of "Example III 99.0

The. medicaments' in' the foregoing preparations are car-- ried-through theouter' layer of dead skin intothe living tissue very rapidly as are the emollients.

Example- V A lotion type emulsion containing'oil and watersoluble emollients and a' thickener also having emollient properties was prepared by'the above described method from the. following ingredients:

Percent by weight Cetyl alcohol 0.75 Propylene glycol 7.50 Isopropyl myristate-palmitate 1.00

Nsoya N-ethyl' morpholinium ethosulfate (35% aqueous solution) 1.00 Water 84.15 Acid stabilized glycerine'mon'ostearate' 4.50 Sesame oil 1.00 Perfume-coloring material 0.10

This preparation is an. opaque creamy lotion having a pH of 3.5. In oven tests at 100 F. and 120 F. it is completely stable for at least 10 days and has a shelf life of over 18 months at room temperature. It may be applied to the skin; and, upon rubbing, disappears rapidly without leaving any oily or sticky-feeling, or agreasy film. This emulsion is percutaneously absorbed and overcomes the resistance of the skin layers to the reception of oils and moisture. Thus, it reduces dryness by introducing oils and water into theliving layers of the skin; and, by soothing the vascular bed where skin rednessis produced, it reduces redness. This lotion: was found to be an excellent .keratolyticagent and a stimulant for the sweat and sebaceous glands and the stratum germinativum. It. equalizedthekeratolyticor sloughrate and the germinativeaction.anrLremovedthe. coarse, dry layers. of skin due tokeratinpersistence. In. addition, it'overcame the damage produced. by exposure. ofthe. skin. to water and alkaline materials, and prevented recurrent damage by these. materials.

The 35 percent aqueous N-soya N-ethyl morpholinium ethosulfate may be replaced with 0.35 percent by weight of the anhydrous compoundv and. the water. content increased.by-.O.65.percent by weight in the emulsion.

Example 'VI A cosmetic creamemulsioncontaining a thickener was prepared from the following constituents:

Percent by. weight Propylene glycol N-soya N-ethyl morpholinium' ethosulfate (35% aqueous solution 1.00

Hydroxyethyl cellulose(3%.aqueousdispersion) 5.00.

Water- 73:.40;v Butyl para'hydroxy benzoate' 0.015. Acid stabilized glycerine:..monostearate 10.00. Sesame 'oil 3.00-

This is an opaque product-having a pH of 3.40 and it is heat stable in oven tests at "F. for one-Week. It' passes into the skin very 'rapidlyand'dries quiterapidly.

Example VII A lotion typeemulsion containing both oil and water Percent by weight: Cetylalcohol 0.75 Propyleneglycol 7.5 0: Isopropyl' myristate 1.50"

N-soya- N-etliylmorpholinium ethosulfate (35% aqueous solution) 1.00. Hydroxyethyl cellulose-('3 aqueous-dispersion) 5 .00: Water 78.1.45 Butyl parahydroxybenzoate' 0.015 Acid stabilized glycerine monostearate 4.50. Sesame oil 1.50

This anopaque. creamy lotionhavinga pH of 3.5 which is heat stable atv 100F. for one week and for sixty hoursat. 130 F. It has very good application properties when in. contact with the skin. The keratolytic and stimulant" properties are good. The hydroxyethyl cellulose and butyl parahydroxy benzoate may be omitted,;ifl desired, and the. watercontent raisedto 83Ll'5. percent by weight to, produce. a heat'stabldopaque creamy. lotion having a; pH of- 3.45

Example VIII.

A. lotion: type emulsion similar to that: descrihedin. Example: above, was prepared from. the. following;

materials:

Percentby weight-v Cetyl'v alcohol 0.75: Propylene glycol 7.5 0.

N-soya N-ethyl morpholinium. ethosulfate (35% aqueous solution) 1.00' Hydroxyethyl cellulose (-.3%.aqueous dispersion) 5.00- Water 78.14

Butyl parahydroxy benzoate 0.015 Peach kernel .oil 3.00. Acid stabilized glycerine-monostearate 4.50

This product is a smooth creamy lotion having a 'pH of 3.45. It isheat stable at100 F. and F. for at least Its dermatological properties are the same stearate, monolaurate,or monopalmitatewhich has been.

9 acid stabilized with from 2 to 5 percent of a salt of diethylaminoethyloleylamide. In each of the foregoing examples the N-soya N-ethyl mc rpholinium ethosulfate was first subjected to the biological assay hereinabove described.

The emulsions contemplated by this invention function in a manner distinctly different from that in which previously known skin lotions or creams have functioned. The emulsions described hereinabove are keratolytic agents and stimulants. They are capable of passing through the normally impermeable barrier of the outer skin and reaching the living tissues of the skin. In doing so they carry along water and emollients which restore the regions that have been de-oiled and dehydrated. Not only is the skin again made soft and pliable but the engorged vascular bed is soothed to overcome skin redness. The keratolytic properties of these emulsions restore the balance between the skin slough rate and the germination rate, and overcome keratin persistence on the outer layer of the skin. This action overcomes roughness and dryness causing callous skin and stoppage of the gland ducts. The stimulating action of these emulsions on the sweat and sebaceous glands and on the stratum germinativum cooperates with the keratolytic action to eliminate excess keratin deposits, and increases the flow of moisture and sebum to the skin torestore its softness and pliability. The emulsions are acid in nature, and, therefore, not only overcome the damage from alkaline materials such as soaps and detergents having a pH of as high as 9.0 but prevent damage to the skin from exposure to water and these alkaline materials. The emulsions prepared in accordance with this invention, owing to the performance of the several functions above described, provide a product which efiectively combats the causes of and relieves conditions of redness, roughness and dryness in the skin, chapping resulting from these factors, hangnail and cuticle roughness and callous skin. In addition, these emulsions have a good appearance and consistency, are highly stable for long periods of time; and, when applied to the skin, have an excellent cosmetic effect in that they disappear rapidly without leaving a sticky, gummy feeling or a greasy film on the skin.

I claim:

1. A heat stable, acidic emulsion having a keratolytic action on the skin and a stimulating effect on the sweat and sebaceous glands and the stratum germinativum comprising from about 0.17 to about 0.7 percent by weight of N-soya N-ethyl morpholinium ethosulfate, said compound being non-irritant to rabbit eyes upon the application thereto of 0.1 ml. of a 1.0 percent aqueous solution thereof each day for five days, from about 3 to about percent by weight of an acid stabilized partial fatty acid ester of a polyhydroxy alcohol and the balance water.

2. A heat stable, acidic emulsion having a keratolytic action on the skin and a stimulating effect on the sweat and sebaceous glands and the stratum germinativum comprising from about 0.17 to about 0.7 percent by weight of N-soya N-ethyl morpholinium ethosulfate, said compound being non-irritant to rabbit eyes upon the application thereto of 0.1 ml. of a 1.0 percent aqueous solution thereof each day for five days, from about 3 to about 10 percent by weight of an acid stabilized aliphatic polyhydroxy alcohol partially esterified with a fatty acid having from 12 to 18 carbon atoms, and the balance water.

3. A heat stable, acidic emulsion having a keratolytic action on the skin and a stimulating effect on the sweat and sebaceous glands and the stratum germinativum comprising from about 0.17 to about 0.7 percent by weight of N-soya N-ethyl morpholinium ethosulfate, said compound being non-irritant to rabbit eyes upon the application thereto of 0.1 ml. of a 1.0 percent aqueous solution thereof each day for five days, from about 3 to about 10 percent by weight of an acid sta' bilized'aliphatic polyhydroxy alcohol partially esterified with a fatty acid having from 12 to 18 carbon atoms, from about 10 to about 15 percent by weight of an emollient material selected from the group consisting of' water and oil soluble polyhydric alcohols and esters of polyhydric alcohols and mineral oil, and the balance water.

4. A composition as defined in claim 3 in whichthe N-soya N-ethyl morpholinium ethosulfate is present in amounts ranging from about 0.17 to about 0.45 percent by weight thereof.

5. A composition as defined in claim 3 in which the N-soya N-ethyl morpholinium ethosulfate is present in the amount of about 0.35 percent by weight thereof.

6. A heat stable, acidic skin lotion having a keratolytic action on the skin and a stimulating effect on the sweat and sebaceous glands and the stratum germinativum consisting of an emulsion comprising from about 0.17 .to' about 0.45 percent by weight of N-soya N-ethyl morpholinium ethosulfate, said compound being non-irritant to rabbit eyes upon the application thereto of 0.1 ml. of a -1.0 percent aqueous solution thereof each day for five days, from about 3 to about 5 percent by weight of an acid stabilized aliphatic polyhydroxy alcohol partially esterified with a fatty acid having from ,12 to 18 carbon atoms, and sufiicient water to prepare a lotion.

7. A heat stable, acidic skin lotion having a keratolytic action on the skin and a stimulating effect on the sweat and sebaceous glands and the stratum germinativum consisting of an emulsion comprising from about 0.17

to about 0.45 percent by weight of N-soya N-ethyl;mor-

pholinium ethosulfate, said compound being non-irritant to rabbit eyes upon the application thereto of 0.1 ml. of a 1.0 percent aqueous solution thereof each day for five days, from about 3 to about 5 percent by weight of an acid stabilized aliphatic polyhydroxy alcohol partially esterified with a fatty acid having from 12 to 18 carbon atoms, from about 10 to about 15 percent by weight of an emollient material selected from the group consisting of water and oil soluble polyhydric alcohols and esters of polyhydric alcohols and mineral oil, and suflicient water to prepare a lotion.

8. A composition as defined in claim 7 in which the N-soya N-ethyl morpholinium ethosulfate is present in the amount of about 0.35 percent by weight thereof.

9. A heat stable, acidic skin cream having a keratolytic action on the skin and a stimulating effect on the sweat and sebaceous glands and the stratum germinativum consisting of an emulsion comprising from about 0.17 to about 0.45 percent by weight of N-soya N-ethyl morpholinium ethosulfate, said compound being non-irritant to rabbit eyes upon the application thereto of 0.1 ml. of a 1.0 percent aqueous solution thereof each day for five days, from about 5 to about 10 percent by weight of an acid stabilized aliphatic polyhydroxy alcohol partially esterified with a fatty acid having from 12 to 18 carbon atoms, and suflicient water to prepare a cream.

10. A heat stable, acidic skin cream having a keratolytic action on the skin and a stimulating effect on the sweat and sebaceous glands and the stratum germinativum consisting of an emulsion comprising from about 0.17 to about 0.45 percent by weight of N-soya N-ethyl morpholinium ethosulfate, said compound being non-irritant to rabbit eyes upon the application thereto of 0.1 ml. of a 1.0 percent aqueous solution thereof each day for five days, from about 5 to about 10 percent by weight of an acid stabilized aliphatic polyhydroxy alcohol partially esterified with a fatty acid having from 12 to 18 carbon atoms, from about 10 to about 15 percent by weight of an emollient material selected from the group consisting of water and oil soluble polyhydric alcohols and esters of polyhydric alcohols and mineral oil, and sufiicient water to prepare a cream.

11. A composition as defined in claim 10 in which c eeses 121 theiN-soyatNwthyl.morpholinium. ethosulfate is present in: the-amount; ofiabout 0.35 percent by weight; thereof.

llcAhheatustable, acidic skinulotion. havin'gfia keratolyti'c. action on; the-skin. and a-stimuhting; effect on the; sweat. and sebaceous.,,gl ands, and the. stratumigerminativumsconsisting of an emulsion comprising, inipercent by igh N-soya N-ethyl morpholinium ethosulfate (35% aqueous solution) L ficid stabilized -glycerine monostearate; 3ato-5" Witter,- q. s;

said N-soya N -ethylmorpholii1ium ethosulfate beingnonirritant ,to rabbit eyes, upon the application thereto of 0.1 mL of a 1.0. percentaqueous solution thereof each day fOIYfLVQKikkYS.

:14. A heat stable, acidic lotion having a keratolytic action; on: the skin. and a stimulating effect on; the sweet 12 and sebaceousglands and the stratum germinativum consisting of an emulsion. comprising, in percent by .weig ht;

Cety1:alccho1 0:75 Propylenmglycoh 7:50? i Isopropyl myristate 1.0.0:

N-soya N-ethyl'; morpholinium cthosulfate aqueous solution) 1.00; Water- 84.15- Acid-I stabilized; glycen'ne monostearate 4t50j Sesame;oii' L001 Perfurne-coloring material 0.101

saidN-soya N-"ethyl morpholinium'ethosulfate being-nonii'ritant to. rab'biteyes upon the application thereto o'fOJl m1; of a 1'.'0 percent aqueous solution, thereof each day' for-five days;

References Citedin-the file Ofthis patent UNITED STATES PATENTS 2 4 11 992.- Niederll Mar. 25, 1947 2,586,288 Appersonv Feb. 19,1952 2,597,260 Reck; May'20,-,1952. 2;71'9 129- Richardson. Sept. 27,1955- OTHER- REFERENCES Pears: .Perf. and Essential Oil. Rev., vol. 44 (March, 1953.), pp. 84-90, 101.

Harry: Modern Cosmeticology,. 3rd ed., 19.47, pp. 152455.

Boatwright: Arn. Perf. and Ess. Oil Rev., v.01. 61,.May- 19,53, 9; 3.61-3.63;

Berf. andnEss. Oil Rev., Vol.59 June. 1952, p. 434. 

1. A HEAT STABLE, ACIDIC EMULSION HAVING A KERATOLYTIC ACTION ON THE SKIN AND A STIMULATING EFFECT ON THE SWEAT AND SEBACEOUS GLANDS AND THE STRATUM GERMINATIVUM COMPRISING FROM ABOUT 0.7 PERCENT BY WEIGHT OF N-SOYA N-ETHYL MORPHOLINUM ETHOSULFATE, SAID COMPOUND BEING NON-IRRITANT TO RABBIT EYES UPON THE APPLICATION THERETO OF 0.1 ML. OF A 1.0 PERCENT AQUEOUS SOLUTION THEREOF EACH DAY FOR FIVE DAYS, FROM ABOUT 3 TO ABOUT 10 PERCENT BY WEIGHT OF AN ACID STABILIZED PARTIAL FATTY ACID ESTER OF A POLYHYDROXY ALCOHOL AND THE BALANCE WATER. 